2-Oleoylglycerol

2-Oleoylglycerol
Names
	IUPAC name 2-O-[(9Z)-Octadec-9-enoyl]glycerol
	Systematic IUPAC name 1,3-Dihydroxypropan-2-yl (9Z)-octadec-9-enoate
	Other names 2-Monoolein
Identifiers
CAS Number	3443-84-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	4478086 ;
IUPHAR/BPS	5112;
PubChem CID	5319879;
UNII	9A2389K694 ;
CompTox Dashboard (EPA)	DTXSID8058661 ;
	InChI InChI=1S/C21H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-20(18-22)19-23/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9- Key: UPWGQKDVAURUGE-KTKRTIGZSA-N ;
	SMILES CCCCCCCCC=CCCCCCCCC(=O)OC(CO)CO;
Properties
Chemical formula	C21H40O4
Molar mass	356.547 g·mol−1
Density	0.958 g/cm3
Hazards
Flash point	> 113.0 °C (235.4 °F; 386.1 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

2-Oleoylglycerol (2OG) is a monoacylglycerol that is found in biologic tissues. Its synthesis is derived from diacylglycerol precursors. It is metabolized to oleic acid and glycerol primarily by the enzyme monoacylglycerol lipase (MAGL).^[1] In 2011, 2OG was found to be an endogenous ligand to GPR119.^[2] 2OG has been shown to increase glucagon-like peptide-1 (GLP-1) and gastric inhibitory polypeptide (GIP) levels following administration to the small intestine.^[2] 2OG has also been discovered to potentiate G protein and not β-arrestin signaling via allosteric binding of the 5-HT2A receptor.^[3]

References

^ Dinh, T. P.; Carpenter, D.; Leslie, F. M.; Freund, T. F.; Katona, I.; Sensi, S. L.; Kathuria, S.; Piomelli, D. (2002). "Brain monoglyceride lipase participating in endocannabinoid inactivation". Proceedings of the National Academy of Sciences. 99 (16): 10819–10824. Bibcode:2002PNAS...9910819D. doi:10.1073/pnas.152334899. PMC 125056. PMID 12136125.
^ ^a ^b Hansen, K. B.; Rosenkilde, M. M.; Knop, F. K.; Wellner, N.; Diep, T. A.; Rehfeld, J. F.; Andersen, U. B.; Holst, J. J.; Hansen, H. S. (2011). "2-Oleoyl Glycerol is a GPR119 Agonist and Signals GLP-1 Release in Humans". Journal of Clinical Endocrinology & Metabolism. 96 (9): E1409–E1417. doi:10.1210/jc.2011-0647. PMID 21778222.
^ Cao, Dongmei; Yu, Jing; Wang, Huan; Luo, Zhipu; Liu, Xinyu; He, Licong; Qi, Jianzhong; Fan, Luyu; Tang, Lingjie; Chen, Zhangcheng; Li, Jinsong; Cheng, Jianjun; Wang, Sheng (2022-01-28). "Structure-based discovery of nonhallucinogenic psychedelic analogs". Science. 375 (6579): 403–411. doi:10.1126/science.abl8615. ISSN 0036-8075.